Synthesis of Unsymmetrically Substituted Bipyridines by Palladium-Catalyzed Direct C-H Arylation of Pyridine N-Oxides

被引:82
作者
Duric, Sasa [1 ]
Tzschucke, C. Christoph [1 ]
机构
[1] Free Univ Berlin, Inst Chem & Biochem, D-14195 Berlin, Germany
关键词
CROSS-COUPLING REACTIONS; BOND FORMATION; BORONIC ACIDS; AZINE; ARYL; 2,2'-BIPYRIDINES; 2-PYRIDYL; FUNCTIONALIZATION; CONSTRUCTION; COMPLEXES;
D O I
10.1021/ol200565u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Substituted bipyridines were efficiently prepared by direct coupling between pyridine N-oxides and halopyridines using a palladium catalyst. Pyridine N-oxides with electron-withdrawing substitutents gave the best yields. This method allows the convenient preparation of 2,2'-, 2,3'-, and 2,4'-bipyridines which are useful as functionalized ligands for metal complexes or as building blocks for supramolecular architectures.
引用
收藏
页码:2310 / 2313
页数:4
相关论文
共 69 条
[41]   Palladium-Catalyzed Ligand-Directed C-H Functionalization Reactions [J].
Lyons, Thomas W. ;
Sanford, Melanie S. .
CHEMICAL REVIEWS, 2010, 110 (02) :1147-1169
[42]   Recent advances in aryl-aryl bond formation by direct arylation [J].
McGlacken, Gerard P. ;
Bateman, Lorraine M. .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (08) :2447-2464
[43]   Highly Efficient Gold Nanoparticle Catalyzed Deoxygenation of Amides, Sulfoxides, and Pyridine N-Oxides [J].
Mikami, Yusuke ;
Noujima, Akifumi ;
Mitsudome, Takato ;
Mizugaki, Tomoo ;
Jitsukawa, Koichiro ;
Kaneda, Kiyotomi .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (06) :1768-1772
[44]   Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of potassium aryl- and heteroaryltrifluoroborates [J].
Molander, GA ;
Biolatto, B .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4302-4314
[45]   First synthesis of caerulomycin B.: A new synthesis of caerulomycin C [J].
Mongin, F ;
Trécourt, F ;
Gervais, B ;
Mongin, O ;
Quéguiner, G .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (10) :3272-3276
[46]   A heterogeneous-catalyst-based, microwave-assisted protocol for the synthesis of 2,2′-bipyridines [J].
Moore, Lucas R. ;
Vicic, David A. .
CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (06) :1046-1049
[47]   Synthesis of 2,2′-bipyridines:: Versatile building blocks for sexy architectures and functional nanomaterials [J].
Newkome, GR ;
Patri, AK ;
Holder, E ;
Schubert, US .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (02) :235-254
[48]   [Ru(phen)2(dppz)]2+ as an efficient optical probe for staining nuclear components [J].
Rajendiran, Venugopal ;
Palaniandavar, Mallayan ;
Periasamy, Vaiyapuri Subbarayan ;
Akbarsha, Mohammad Abdulkader .
JOURNAL OF INORGANIC BIOCHEMISTRY, 2010, 104 (02) :217-220
[49]   THE ACTION OF HETEROCYCLIC N-OXIDES ON 2-BROMOPYRIDINE - OXIDATIVE BROMINATIONS INVOLVING N-OXIDE HYDROBROMIDES [J].
RAMIREZ, F ;
VONOSTWALDEN, PW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (01) :156-160
[50]   Small Molecule-Based Binding Environments: Combinatorial Construction of Microarrays for Multiplexed Affinity Screening [J].
Roska, Rachel L. Weller ;
Lama, Tenzing Gawa Surshar ;
Hennes, Jay P. ;
Carlson, Robert E. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (46) :16660-+